Pros
The people are (or were) the best thing about Playboy. The work environment was generally casual. The holiday parties were pretty fantastic for the first few years. Sometimes, you have travel opportunities. You occasionally meet models and celebrities.
Cons
The corporate part of this company often threw employees under the bus. The pay was on the low end of the median. Holiday bonuses? Forget it, because Christie Hefner "didn't believe in them", so now it's corporate policy. Every few years, there were rounds of unneccessary layoffs instead of CEOs and VPs taking paycuts, they were getting raises and golden parachutes. During my last few years, the company started converting into an "intern factory" to save more money. People continually left the company, wanting to leave a "sinking ship". After bringing the company private, the biggest mistake they made was moving production outside of the US and closing the Chicago headquarters.